I met my first girlfriend through Windows 95: An Internet love story

Before everyone dated on the Internet, "pioneers" confused parents and peers alike.

Nearly 19 years ago, I said "I love you" to a girl, face-to-face, for the first time. It's a moment I remember clearly: Flowers. A ring. An awkward kiss. Both of our moms hovering around since each had driven us three hours to a halfway point.

It was weird like any early teenage romance, but this particular iteration of adolescent awkwardness remains unique even in retrospect.

My "I love you moment"—like any sense memories from my teenage years of 1996-98—mostly revolves around my bedroom. Here I hid from the feeling that I didn’t fit in at my high school, from feeling inferior to my siblings, from my parents’ dissolving marriage. And luckily I had quite the hiding place: a nook on the room’s far wall, sectioned off in such a way that the light from a single window, the sound from a nearby stereo, and the glow from an overweight CRT monitor filled the whole space.

The nook had a built-in desk that was perfect for the Pentium 166 computer our father had bought for the family earlier in the year. My older, sports-loving brother would barge in here on occasion to load a Tony La Russa baseball management simulator, but otherwise this was my largely uninterrupted personal space. Forget the sights, I can still hear my Pentium space: modern albums by The Chemical Brothers, REM, and local favorites The Toadies; dial-up tones—especially the rare, shrill interruption when a call-waiting beep or picked-up phone would interrupt a connection; and furious typing on a chunky, “quiet-type” keyboard, where I averaged the same 100 WPM rate I maintained with occasional Mavis Beacon CD-ROM lessons.

This I where I really remember her, Vivienne. Vivienne was the first girl my age to say she loved me, and she existed for a few months as little more than a voice, a few blurry photos, and seemingly endless pages of typed words. I was smitten, determined to meet her in person one day.

Almost two decades later, I wonder how often this kind of love story popped up around the United States in the mid-‘90s. Windows 95 was the icing on the home-computer cake, and the decade’s rise in affordable computing was met with a plummeting Internet learning curve. Web browsers were maturing, online services were exploding, and public interest was peaking.

And curious people, particularly younger people with time to spare, were finding ways to connect to each other in a way that will forever be specific to the era. Before the mid-‘90s explosion of dial-up ISPs, long-distance connections made through computers certainly existed but largely as fringe cases. By the year 2001, family Internet access had become more commonplace, and Internet communication protocols like ICQ and AIM became standard fare. Around the turn of the century, anecdotal evidence suggests it didn’t take long for American kids to depend on Internet methods for talking to local friends.

Enlarge/ (Editor's dramatization, this isn't young Sam with his Pentium 166...)

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But between those two personal computing eras, there we were, a scattershot assortment of other teens and me chatting through that weird, in-between growing-pains period. I’d always loved computers, but I didn’t grow up in a family where computing was prioritized—or understood—by my parents. The same could be said for most everybody else I eventually met this way. We chatroom denizens put just enough pieces of the puzzle together to find each other over the Internet, and nobody else in our respective cities—our parents, our teachers, or even our classmates—had done the same.

We felt like pioneers. We were the people learning about computers with little prior encouragement and without the help of things like hometown hacker clubs. Finding like-minded people across the country made us such technology converts that we did crazy stuff—like convincing our parents to drive us across the country so we could meet awkwardly in a motel parking lot. And the love in these late-'90s chatroom love stories—much like those in any other classic, misunderstood-teen saga—burned bright. This was paradise by the CRT monitor light.

Blood on the motherboard

My ‘80s upbringing didn’t include many cultural touchstones. Our family simply didn’t live anywhere long enough to set roots in a major community or religious organization (or, heck, even the Boy Scouts). Due to work promotions, my father had moved us three times by the time I was six years old, at which point we landed in the kind of Texas suburb that disappointed my elementary school penpals. The town had no cowboys or horses to speak of, nor did it really have southern drawls, visible gun-rights advocates, or most other Texan clichés. It did have many well-to-do doctor/lawyer/dentist families who held Ronald Reagan and George H.W. Bush in the highest of esteem, not to mention giant, affordable lots of land that, to this day, make me wonder if we’d moved to some sort of Poltergeist-style development.

Either way, our five years in that suburb ended after fourth grade. There was another move—and another move the following summer. The shake-up did no favors to my siblings or me, both scholastically and socially. Out of everyone, I struggled the most to fit in once we set roots in the Dallas-area municipality of Highland Park. (It’s as rich and conservative a place as I’ve ever lived, and you can learn more about it here.)

The short version is that I’d moved somewhere with a defined culture—one of wealth and deeply conservative values—and didn’t fit in. My outsider feeling lasted through most of my middle and high school career, and though I dealt with it by hiding with comics, video games, and books, I was also hungry to make friends. I’d always had the social-butterfly bug—I was the kid who would strike up conversations with strangers, much to my parents’ chagrin—but instead of racking up new friends, I just came off as an easy, uncool target and got picked on accordingly. (You know, chased around the locker room by bullies while I was in my underwear, that sorta thing.)

I also didn’t grow up with a home computer; my parents thought an NES and a “word processor” typewriter were plenty. As a result, I soon pretty much lived at my schools’ computer labs—especially at lunch, so that I wouldn’t have to deal with being the kid who sat alone. At the labs, I recall typing out BASIC programs from issues of 321 Contact, dabbling in early LAN computer games like Bolo, and teaching myself how every little menu and option in Windows and Mac OS worked.

For whatever reason, my father changed his computer tune in early 1996, at which point he went to a mom-and-pop computer shop to buy a custom-built Windows 95 machine for the family. Initially, he elected not to add a modem to the machine—'what did we really need that for?' he rhetorically asked.

I soon did what any kid would do in such a situation. Two months later, I went behind the family’s back and used my saved-up allowance to buy a 28.8k modem from a kid at school. His father had just upgraded to the breakneck speeds that 33.6k could deliver, so he fished out the old modem from his dad’s office and pocketed my $50. I alternated between reading the cryptic modem instructions and learning from my own trial-and-error to find the right jumper and BIOS settings—I’d once gotten a Sound Blaster to work with the computer game Jazz Jackrabbit, so I was qualified enough, I figured. Eventually, I installed the US Robotics modem without shorting out the entire system. (I did cut my hands navigating the crowded motherboard, however. I recall thinking of the blood as part of my computer initiation ritual.)

With an AOL free-trial CD-ROM, I confirmed that the modem could work and connect my computer to the World Wide Web... but not much else. Turns out you needed a credit card to cash in on AOL’s free dial-up Internet trials—same with Prodigy and Compuserve, too.

But I was determined to get online, even though I really didn’t have an answer to my father’s rhetorical question. What did I really need it for? Shit, I had no idea, but I’d seen screens and commercials hinting that the Internet was a portal to something new. I had a hunch that, like every other computer-related thing I’d ever used, I would love it. And as luck would have it, a clerk at the very oddly named shop near my school, Software At Cost Plus 10 Percent, had an idea: ever heard of beta testing?

Some new startup ISPs needed testers before they launched paid Internet service in the Dallas area, the clerk told me, and one service in particular had sent a rep to the store recently. He told me to come back a week later, and when I did, I found a stack of free beta-testing invites to why.net—a long-gone ISP whose remnants are still up at the Wayback Machine—along with instructions for how to connect to the service via Windows 95’s clunky internal dialer. I rushed home, made sure nobody was around to pick up the phone, and successfully dialed in.